Where Men Saddle Up and Ponies Paddle Over

Wayne Estes woke up before dawn on the third day of his vacation, scarfed down an egg sandwich and doused himself in bug spray. He bucked the heat, putting on his spurs, leather boots, jeans and long-sleeved yellow shirt. Then he settled into the back of his red “cowboy Cadillac” pickup for what is, every year, the ride of his life.

It is a ride that either breaks or warms little girls’ hearts, as Estes and his fellow “Saltwater Cowboys” round up the wild ponies on Assateague Island and drive them to swim across the channel to the small neighboring island of Chincoteague, where a lucky few were able to buy the foals at auction Thursday.

For the 40 or so cowboys who ride alongside the ponies every year, it’s a lot harder than it looks.

“There’s a lot of mosquitoes, a lot of mud, and the deerflies are bad,” said Estes, who owns an auto repair business in Chesapeake, Va., and participated in this week’s ride. “But it’s a dream come true that most people would love to do and are just never able to do it.”

Every year, Chincoteague’s annual pony swim draws 40,000 people -- many of them young girls -- to an island forever intertwined with its equine neighbors.

Since the 1600s, wild ponies have roamed the beaches of Assateague. Local lore has it that they came from a Spanish shipwreck, but in reality they are probably descended from animals owned by colonial settlers who allowed them to graze on their land.

The pony swim officially began 81 years ago as a fundraiser for the Chincoteague Volunteer Fire Department, and it has become an effective means of thinning the herd.

Chincoteague’s minutes of fame require days of blood and sweat from the cowboys.

Every year, the crew rounds up dozens of ornery ponies in the woods and corrals them into a pen, where a veterinarian checks them to see whether they’re fit for the channel swim.

The air is usually thick with biting flies, the water with stinging jellyfish. The horses sometimes cut their hoofs or get stuck in the mud. And the cowboys, some of whom are in their AARP years, have to be careful they don’t throw out their backs or mess up their knees.

Though Wednesday’s swim didn’t start until nearly 11 a.m., the crowds began staking out the high ground in the marsh shortly after midnight. Many stood in the bug-infested salt water for hours, waiting for the five-minute swim and subsequent parade through town.

Girls in bikinis stood alongside women in bonnets and full-length dresses to greet the ponies that strutted down Beebe Road, led by two red pickups and a squadron of cowboys.

Some spectators are just horse people. Michigan native Andrea Galbraith, 21, is studying equestrian management and working on a horse farm outside Philadelphia this summer. When she found out she had a few days off this week, she gassed up her Dodge Durango and headed for the Virginia line. With hotel rooms unavailable, she’s sleeping in her car.

“It’s kind of a little girl’s dream to come to see the ponies, but it’s never been possible until now, when I had the gall and the vehicle to get there,” she said.

Though pony-penning has been a tradition since the 1920s, it wasn’t until author Marguerite Henry’s 1947 children’s classic “Misty of Chincoteague” that the swim and pony auction became an international attraction.

Much has changed on the island since Misty’s time. Tiny, weathered cottages have given way to expansive waterfront homes. Souvenir shops abound, and nearly every hotel for miles around is booked during the last week in July.

What hasn’t changed much are the cowboys. Year after year, the same few dozen guys -- and they are all guys -- come back to Chincoteague for what feels like a family reunion. About half are with the Fire Department. The other half come from Virginia, Maryland and as far away as Florida.

Some grab local hotel rooms and frequent bars such as AJ’s, where the bartender fixes screwdrivers for both the cowboys and their horses.

A few park their motor homes on private property in town, where a makeshift stable advertising “margaritas, martinis and bikinis” keeps their canned beer cold.

Delmas Taylor has been riding for 23 years.

Ed Reynolds, who at 60 calls himself “the senior citizen of the group,” has been doing it for 10.

Both helped get their sons spots as cowboys, but having a father in the fold is no a guarantee -- as most cowboys tell it, someone has to retire or die for a spot to open up, about one a year.

Many, many more people than that ask to join the cowboys.

But it takes years of work to get in.

A Defense Department worker from Bedford, Va., Reynolds got his job the old-fashioned way: He started at the bottom, manning the gates and watching the pony pens.

After four years, he got his chance to ride.

Pony-penning day is always the last Wednesday in July, rain or shine.

And some years have been tough. Sometimes it rains all day. Sometimes a horse -- or a man -- gets hurt in the mud and muck.

Former cowboy Sam Mitchell remembers one year when the mosquitoes were so thick he had to wipe his hands on his horse’s neck as he rode.

The most memorable times are those years when a crestfallen little girl who can’t afford to buy a pony ends up with one anyway -- either the crowd donates the money or her parents break down and go over their budget.

On the parade route, there were many lovelorn little girls, watching as the cowboys waved to the crowd between checking their cellphone messages and passing around a water bottle.

After a long, sweaty morning, they were soaking in the adulation.

None looked more macho than Edwin “E.T.” Taylor, who rode his horse while puffing on a pipe packed with Captain Black tobacco -- the better to keep away the mosquitoes.